


Maybe, Probably: The Awkward Dates of Leon Kuwata

by IsTheMedia



Series: Hope's Peak Failures [2]
Category: Dangan Ronpa: Trigger Happy Havoc
Genre: Grinding, Implied/Referenced Alcohol Abuse/Alcoholism, M/M, Multi, Other, Self-Doubt, Self-Esteem Issues, Wet Dream
Language: English
Status: In-Progress
Published: 2019-04-03
Updated: 2019-04-11
Packaged: 2020-01-04 09:39:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,361
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18341051
Author URL: https://archiveofourown.org/users/IsTheMedia/pseuds/IsTheMedia
Summary: Hope's Peak Academy. The school of dreams. The school where your life is guaranteed when you graduate.....what a crock.**HIATUS**





	1. Chapter 1

**Pt 1.**

Fuck he felt great! He couldn’t BELIEVE how tonight’s show went. He hoped that this would help him even MORE with getting noticed. He didn’t know what was so different about this time?

What caused him to be so--

“Not bad Kuwata.”

Shit...that was it wasn’t it? He looked over his shoulder to see him there. It was still so weird to see him without the pomp...but damn he wore the updo so damn well. “You some kinda critic?” He teased. Where was Taka though? Was weird to see one without the other.

“C’mon, wanna drink? Think ya deserve one after a show like that.”

He’d ask later. One drink lead to two.

Then three.

Then five.

And that’s when Leon realized how fucking needy he was when drunk. Pawing and almost trying to climb into Mondo’s lap. The biker didn’t seem to mind much. Wrapping an arm around him to keep balance on the stool.

A mouth on his neck and Leon was far gone. Moaning and pleading for Mondo to do something. To get out of here…

He wanted to fuck. How he wanted the biker’s dick.

It felt like he was somebody completely different now, and for the life of him Leon didn’t care. He felt so good to be this open.  

He was slammed up against the door. Leon opened his mouth to remark on how it hurt, but Mondo’s mouth was on him in an instant. Teeth biting at his lower lip, and Leon couldn’t help but moan as he opened his mouth.

Those warm hands-shit Leon could FEEL the heat through his jeans-grabbed him under his thighs and hiked him up, feet no longer touching the ground. And shit! That was such a turn on.

The pathic whine that left him, Mondo fucking loved it; he could tell ‘cause he felt the biker’s lips quirk up into a smirk against his own. Mondo urged Leon to wrap his legs around his waist as he pressed closer. He moaned as thier hips were pressed together-holy shit did Mondo FEEL bigger than the last time? Leon barely had time to even consider it before Mondo rolled his hips, and the sparks that shot up his spine had his mind go completely blank for a moment.

Getting off in a club’s storage room?

Shit that can get checked off the list.

Mondo was grinding into him, and fuuuuk it felt so good! He knew he was a whining and whimpering mess-but fuck it who cared anymore! Hips trying to buck into the biker’s, as those warm hands kneaded at his ass.

He was expecting Mondo to make a snide remark about him not really having much back there, so when he saw Mondo open his mouth and surged forward and kissed him. The guy really seemed to be into his piercing. Sucking at it and just groaning whenever he would run it along Mondo’s tongue or the roof of his mouth. Heh, maybe he could talk the biker into gettin’ one too?

There was a deep growl and--

OH SHIT!

  
Leon didn’t know he could have been pressed up even MORE to the wall, but Mondo proved otherwise.

Teeth were biting along his neck. And Leon was losing it. He whimpered as he felt Mondo bite and tug at at one of his earrings. Hips bucking at the action.

“Ya like that?” Mondo growled in his ear, and Leon could not hold back his moan as the biker ground into him harshly. “C’mon, I know yer louder than this...lemme hear ya.”

Leon threw his head back ignore the bright flash of light behind his eyelids has he head hit the door with more force than he intended. Mouth hanging open drooling slightly as he moaned openly and loudly.

“Yeah, fuck,” the biker rolled his hips harder. “Jus’ like that...betcha they can hear ya.”

The up and coming musician was so lost in the fog of pleasure that he forgotten where he was for a moment. R-right, shit he-he was still at the club.

Mondo ran his tongue along the tight, nearly protruding tendons in Leon’s neck. “Like that huh? Ya want them ta hear ya? This door’s shit at keeping noise out...ya can hear ‘em nice and clear can’t ya?”

Leon cried out as he clenched his eyes shut. And fuck, he could...he could hear the crowd outside.

“Betcha they can hear ya too,” Mondo continued. “Hearin’ ya moan like a bitch. Probably turnin’ some on too.”

Leon cried out again and tightened his hold onto Mondo. Fuck fuck! He didn’t care if they heard them. He was close...so close!

The crowd outside did nothing to quell it. Their cheering and screaming…

Wait...that wasn't screaming.

That sounded like...blaring?

\--

Leon’s eyes snapped open, as he tried to catch his breath. His alarm clock blaring besides him.

A-a dream?

H-holy fuck did he have a wet dream about Mondo?!

Groaning softly he pushed himself up, letting everything around him come into clearer vision. He grimaced as he felt something cooling and damp between his legs. He buried his face in his hands and let out a muffled scream. He fucking CAME from a wet dream!

Sitting there for a few moments, just letting the dream replay in his head.

Dammit...he thought he was done with this after-ah-g-getting together with them. But here he was. Hell he can’t even remember that last time he HAD a wet dream that intense!

Huffing some he tossed the blankets off of him and made his way to the bathroom to clean himself up.

He stared and just watched the water run down the drain...almost an echo to his last fantasy he had of Mondo. Though this time he wasn’t in that perpetual state of questioning himself. Questioning his sexuality-well as much.

It still felt too good to be true...especially when he’d wake up and be at his own place. Part of him wanted to stay at their place more, but he couldn’t do that. It was more than enough for them to even give him a chance. To keep him around.

Leon was just counting the days until they left him. He knows it was going to happen. There was no way he could stay with them. Bad enough Taka already had a rep with his name but with him being open about his relationship with Mondo?

If Leon popped up too then that would be it for him.

Political suicide.

Shaking his head he turned off the water and made his way out. Stripping the bed clean--he really didn’t have much for extra blankets and such, just stuff that have been packed since leaving Hope’s Peak but it’ll do.

He settled in and looked to his phone laying in the bedside table. His mind contemplating on the next course of action. Neither of them would even be up…but he was already reaching for the phone.

 

_Hey…_

_Miss u 2_

 

Leon buried his head under his pillow as he yelled. Stupid, stupid, stupid! Why did he even send it!? He was such a fucking mess! Too busy with his berating of himself, Leon didn’t even notice there was a reply.

 

_Miss you too._

_...dinner? Tomorrow?_

_-Kiyotaka Ishimaru_


	2. Chapter 2

**Summary for the Chapter:**

> SFW
> 
> Double Date
> 
> Hinted Past Alcoholism

**Pt. 2**

  
  


Although Leon was still unsure how to go about this whole...relationship? Holy fuck...that's what this whole this one was now, wasn’t it? He couldn’t even remember the last time he had a more than one night stand. He thought that this couldn’t get any weirder. 

And then Taka began planning dates for the three of them. 

Leon had no idea how to even deal with that. It’s not like he HASN’T gone on any dates, just...this was different. God fuck, part of him always felt so-excited?-like this was something he was waiting for. 

Damn, maybe he did like Taka way back then. 

But...this?

This...was so damn awkward. Like, really fucking awkward. Leon wasn’t sure what to expect when Taka said that they were inviting some...others with them to dinner. Apparently it being a thing the moral compass had planned out. 

But it looked like Taka, even with all his planning and forethought couldn’t foresee THIS happening. 

Leon had to admit it was awesome seeing Makoto and Kyouko again. Kyouko mentioning how she’s heard about Leon becoming a regular at the club-and how she can be sure that it’ll only be the beginning for him. 

Shit, hearing that from the girl known as the Ultimate Detective felt hella amazing. And Makoto? Shit dude hasn’t changed a bit! Polite as ever...and well thanks to Leon’s personal self reflection, he can say that goddamn the lucky student was still cute as ever. Like it felt so damn GOOD to know he can think that guys are cute or hot, and think the same about chicks and it’s cool. 

I-it can be normal. 

However, it was who was with them that had things turn a bit...awkward. 

At first Leon had to do a double take, because--no, just fuck no! He didn’t even know the guy owned, well, any clothes that WASN’T a suite! Sure Chi text him about some articles about some shit going on with the Togami family….

Buuuuuut he didn’t read them. Not like he cared about Byakuya in the first place, so why should he? 

Well...that fucking changed real fast. Because now, he was sitting with the dude. It was weird enough to have him suddenly joining in; but the place they were having dinner at? It sucked at seating for more than four at a table. 

So one table had Mondo, Taka, Kyouko, and Makoto seated at, and just across the way, was Leon and Byakuya. Leon tried to avoid to make this even more uncomfortable by looking through his phone and NOT at the affluent progeny . Taking time to ready the dang articles he neglected. 

And holy shit…

He didn’t know how to react at what he was reading. 

Eye darting from his phone to Byakuya and back again. He opened his mouth--

“It’s true you idiot. Perhaps next time you actually decide to read on things Fujisaki provides to you rather than just omit them right away.” 

Leon closed his mouth. So...Byakuya Togami, was officially disowned. Holy shit, seems like he wasn’t the only one who had the “promised future” taken away from him. Shit was it? Like he could still be the Ultimate Affluent Progeny, right? Cause didn’t he say his well-being was a free-for-all? Goddamn why was he even bothering?!

Leon glanced over to the other table, he really couldn’t hear what was being talked about, but Taka was smiling, and Mondo laughed...Makoto’s face was a bright red. Eyes darting to the other, the up and coming musician could only stare. 

Byakuya was looking over too...with soft eyes. The corner of his mouth slightly curled in a partial smile. 

Shit...guy was looking like he was seeing the secret of life or something like that.

Did he...was he really no longer that damn title?

“Shoulda figured it out,” Leon said under his breath. 

“What could you have possibly figured out?” Byakuya asked curtly, eyes looking over-and yep that’s the glare he’s always seen. 

“That ya liked them. I mean….you sorta did show a soft spot for ‘em,” Leon shrugged as he took a drink of his water. 

“I have no idea what you are talking about,” the former affluent progeny  huffed. 

“Dude, each time somebody tried ta make a suggestion fer the class ya shot it down,” Leon began pointing accusingly at him. “But if like Kyouko or Makoto said the same damn thing ya didn’t say a word.” 

There was a beat of silence, and heck yeah he felt proud. Like he shut up the asshole fer onc--oh shit! Dude was blushing! 

Byakuya scoffed and looked away as he adjusted his glasses, and sure enough there was a slight tinge of pink dusting his cheeks. 

There weren’t many words shared between them until their entrees arrived. It was still just so weird. It...didn’t feel quite like a date in Leon’s mind-even though Taka and Mondo did keep glancing over to him. He’d smile and give a slight wave or thumbs up...h-he didn’t want to ruin their time. They really seemed to be enjoying themselves. 

Looking back to who he was seated with, he did have to wonder at Byakuya’s choice of drink. Surely dude woulda gone for some sorta fancy wine with it…not some weakass tea.

“Is there an issue?” 

Leon jumped, shit how long was he staring? 

“Well?” 

“Nah just...um…”

“Then stop staring, you’re making me lose my appetite.” 

“Jus’ use ta ya complainin’ ‘bout bad tea,” he shrugged as he took a drink of his beer. “Figure guy like ya would still wanna have some wine or shit with your dinner.” 

“...I do not drink.” 

Leon almost choked. Why the hell did that sound so, hesitant? This WAS Byakuya Togami! The dude NEVER hesitates on anything! “Ya...don’t?” 

“I do not, drop it,” Byakuya snapped. 

“Alright alright,” Leon held up his hands defensively. “I mean, I get that drinkin’ isn’t somethin’ everyone likes--” 

“Kuwata, I know what you’re doing,” Byakuya said, voice low and eyes narrow. “It won’t work.” 

Leon shrugged. “I mean it’s weird yeah, but I mean if ya can’t handle--” 

There was a slam on the table that actually had him jump and he could almost FEEL the heat from Byakuya. “I’m...recovering,” the other admitted through grit teeth before he stood up and promptly walked away….and eventually out the door. 

It took a few moments before it registered with Leon...oh fuck...OH FUCK! He was already scrambling to go after the other, even before Taka could ask him what just happened. 

Stupid stupid-- “Hold up!”

He swore Bayakua woulda slapped him for grabbing him but--he didn’t. Guy looked…

He looked like he was ashamed. Like completely. Leon let go right away. T-this was just too weird. Almost too much. 

Shit, maybe Hope’s Peak fucked people up more than providing a good future for them…

“S-sorry dude...I--fuck,” Leon rubbed the back of his neck. He was apologizing to fucking Byakuya Togami! He thought he’d never see the day. 

“Satisfied? Seeing me in such a state must be a joy to you.” 

Leon blinked. “The hell? Dude! The fuck is yer problem!?” 

“Don’t play dumb, even though I know you’re very good at i--” 

“Nah nah nah, you listen up! I didn’t give a single FUCK about ya,” Leon began as he pointed at the former affluent progeny. “Like I thought the most was you havin’ a hissy fit like always in high school! And ya know what? Yeah I was fuckin’ wrong in assumin’ that shit!” 

Byakuya opened his mouth to retort but Leon continued on. 

“The moment I saw ya I thought mine an’ Taka’s an’ Mondo’s night was fucking done! Cause yeah, ya kinda always pulled that shit! But now I’m readin’ all this stuff and -and---fucking hell man! Why didn’t ya tell ANYONE else!?” 

“Because, as you stated, you don’t care,” Byakuya stated coldly. 

Leon groaned as he rubbed at his temples. Shit, he did say that. B-but he didn’t mean it like that! “Alright, yeah I said that, but you damn well it ain’t what I meant.” 

“Oh, then tell me what you did mean?” Byakuya asked as he crossed his arms. 

He bit his lip as he tried to stare the other down. “Cause c’mon man...we spent 4 years tagether. Would like ta think there was some connection made.” 

Byakuya scoffed. “I was wrong, you don’t play dumb too well. You are just that dumb naturally.” 

“Oi! I’m tryin’ ta apologize here at least! Cut me some slack!” Leon yelled. “Ya ain’t alone in this! Yer not the only one who’s—”

“You cannot POSSIBLY comprehend what I'm going through! YOU chose not follow your talent!”

“I’m goin’ through OTHER shit though! And I’m still confused by it!” 

Byakuya scoffed. “I’m not all that shocked. You would be confused by a lo--”

“Doncha even get why I’m here with Taka and Mondo?” Leon cut him off. He wasn’t in the mood to keep fighting; despite that being what Byakuya wanted. 

“Because of this  _ confusion _ ?” Byakuya shot back with air-quoting ‘confusion’.

“Yeah but yer so smart you can tell me then,” Leon crossed his arms. 

Byakuya stared at him for a bit. What, was he not getting it? Dude ACTS like he’s so smart. He kept waiting...seemed like Mr. “I’m-better-than-everyone” really didn’t know. 

“Is this still on about Maizono rej--”

“Holy shit you don’t get it!” Leon swore he coulda pulled something at the eyeroll he gave. “I’m fuckin’ WITH them.” 

“I was aware of th--”

“Dude! Like you are with Kyouko and Makoto!” 

Oh...well that shut him up right quick. 

“...I see...maybe you COULD have a vague comprehension after all.” 

**Notes for the Chapter:**

> This along with "The Unlikely Friendship Story of Touko Fukawa and Yasuhiro Hagakure " and one more to be posted soon (ie Part 4 of this series) all sorta correlate in the same time frame just focusing on different people.


	3. Chapter 3

**Summary for the Chapter:**

> Taka invited Leon over. He just assumed it was going to be a...typical...night? Um...where was Mondo?

**Pt. 3**

 

Leon was making his way up the stairs in Taka and Mondo’s apartment complex. Passing said biker as he headed down. Mondo gave him a grin and continued on down, not even stopping for a moment. Leon watched until Mondo turned the corner and was out of sight. That was...weird?

Maybe dude was in a hurry? But he didn’t seem to be rushin’ down the stairs...

Where the hell was he goin’? He shook his head and continued up. He could ask Taka…

He hoped it was nothing bad.

What was he thinking, Mondo looked happy or at least not pissed. So yeah!

Unless...maybe it was Taka who was mad? And that grin was him giving a ‘ _good luck_ ’. Shit! D-did he mess up an evening?!

N-no...he was invited over. S-so what was going on?

Leon sighed as he knocked on the door and prepared himself.

“Come in! I’m sorry I’m a bit busy at the moment!” Taka’s voice called back.

Leon felt the corner of his lips quirk up into a half smile. Goddamn he didn’t even know what the other was doin’ and he was just thinkin’ how cute he HAD to be! Without waiting any further he stepped in. The place looked insanely clean as ever.

“Ah! You came,” Taka greeted as he set down the laundry basket. “Did you eat?”

“Ah...y-yeah I did, so I’m good.”

“It’s just going to be us tonight,” Taka stated.

“Y-yeah saw Mondo on my way up,” Leon began. “Um...y-you two ain’t fightin are ya?”

“Wh-what? Why would you think that?”

“I-I dunno! I mean I...well I thought when ya invited me that we were all gonna...you know...um…”

“Mondo and I did not have a fight, something came up,” the former moral compass explained.

“So not in a fight?” He should have assumed that. Mondo was grinning on his way down, and the more he thought about it, it looked so genuine.

“Of course not!” Taka almost sounded offended.

“S-sorry Taka, just...wasn’t sure.”

The harsh look left those red eyes, and then he gave a soft smile. “The guys wanted him to join them for a ride. Even though he’s not a Diamond anymore, they are still his family. I would never want to keep them away from that.”

Yeah ok that made sense. Man he shouldn’t try ta think about what-ifs especially with how this whole thing is...really wasn’t helping him make this easier. If they has a problem they would tell him…

Right?

Before he could spiral into another bout of self-doubt, Taka pulled him out of it. Asking him how his day went and such. It was a simple evening. A drink and simple talking. It was...nice. Like really fuckin’ nice. Sorta gave him flashbacks to Hope’s Peak. Goddamn seeing Taka’s face light up when he was happy was amazing.

As the night went on Taka said he was going to get a bath ready…

And then asked if Leon would join him.

And Leon KNEW there was no fucking way he would have declined.

It seemed innocent enough. Hell, Taka was like this even back in high school Really didn’t get how...intimate this really was. But he insisted...didn’t help he brought up how he and Mondo do this often. God fuck that brought up some images in his head…

Some really REALLY nice images.

The tub was filling and as it did Taka was disrobing. Jeeze even when taking a bath the guy folded his clothes.

Fuck it was cute.

When the water was high enough Taka insisted that Leon get in first. Leon was about to argue but went against it and got in. The water was warm and the tub was soooo much bigger than the dinky thing he had at his place. He let his eyes closed and tried to relax a bit.

But he should have known better.

There was a sudden sound and water splashing.

Opening his eyes, Leon tried to keep his breathing under control as Taka settled between his legs. His heart hammering against his chest. Goddamn, he looks so good. Like he knows it’s cliche as fuck, but Taka did look almost ethereal like this. Pale skin, with droplets of water that added to the unreal quality.

Taka flashed him that smile as he settled in and the musician tried his best to not pop a boner. Th-this wasn’t MEANT to be sexy but fuckin’ hell, there was Taka wet and naked between his legs!

“Are you alright Leon?” Taka asked as the other began to wash himself.

“Y-yeah! T-totally fine!” Leon responded, voice tight.

“Hmm?” Taka looked over his shoulder to look at the other. Leon knew his face had to be a bright red. “Are you sure?”

He could only nod, he tried to reach around the other so he could focus on something OTHER than Taka’s AMAZINGLY muscled back. But instead, Taka grabbed his arm. Leon didn’t mean to yelp, but it caught him off guard.

Taka shifted some and pulled Leon closer, and then--

Geeze did he always have to whine into the kisses he got? But it was just...so good. Soft and warm. Slow and deep. Taka’s tongue was slowly mapping out Leon’s mouth, running over his own, and along the roof of his mouth.

They pulled apart long enough for Taka to turn around, and was now facing Leon, still settled between his legs.

He leaned in and gave Leon another kiss. Leon didn’t realize he was clutching onto Taka’s biceps so tightly. Dude was gonna have bruises.This one didn’t last as long as the other, but it didn’t matter, as Leon felt that hot mouth trail down his neck. A hand was trailing down his chest.

There was a flash of self-consciousness that ran through Leon’s head as he felt that hand on his chest. Wasn’t like he DISLIKED his body, fuck no. He liked it-hell HE’D fuck himself if he could…

It was just…

He wasn’t “fat” but he wasn’t “ripped” either. There was muscle sure, but it wasn’t defined like Taka’s or Mondo’s. There really wasn’t much to i--

Taka’s hand brushed against one of his nipples and Leon arched up into the touch.

Fuck!

Right he had THOSE at least.

“I wanted to see what I could do with these,” Taka said, voice steady still-so not fucking fair! “But I didn’t get the chance,” he continued as he flicked one of the barbells that ran through one of Leon’s nipples.

Yeah yeah this was good. Fuck more than good!

Leon squirmed a bit as Taka tugged and rolled the piercing for a bit. He was getting hard and he KNEW that was what Taka wanted. He played with it for a little while before he brought his mouth down to the other.

The cry that left Leon should have embarrassed him, but his mind was abuzz with just FEELING that hot wet mouth, and he couldn’t be bothered! The water in the tub sloshed around some as Leon’s hips bucked up, just wanting some stimulation.

Leon was so distracted with what Taka was doing to his chest he didn’t realize he lost track of the other’s hand, until he felt it reach between his legs.

“May I?” Taka breathed, breath ghosting over the nipple he was sucking on just moments earlier; and Leon could just nod as he tried to shift to open his legs a bit more. He could hear water sloshing out of the tub and onto the floor. But it seemed that Taka didn’t mind it.

Leon’s hips bucked as he felt a finger run against the whorl of muscle. Teasing it slightly until the up and coming musician was whining again.

“I don’t have any--”

“ ‘salight,” Leon cut him off, his voice a bit breathless. “Just...k-keep goin’.”

“Are you su--”

“Please,” it came out as more of a cry than anything else. Taka took that as the go ahead and slowly, painfully slowly eased a finger in.

Leon moaned softly. H-hot. He couldn’t help but squirm at the feeling. Taka hushed softly as he pressed up closer to him. Kissing him again, trailing those kissed to his neck and then up to his ear where he toyed with one of the many piercings.

For a moment Leon couldn’t see! It was all so much and it was getting almost TOO hot for him. Then, a second finger was joining the first. He bit his lip as a loud moan tried to break through as he felt water seep inside as Taka scissored his fingers, stretching him.

“You’re so loud Leon,” Taka observed.

Heh, Mondo said that too...did they like it?

Taka curled his fingers just right and--and--!

\--

Leon felt his body jump as he awoke. Chest heaving mind racing. His body felt hot and sticky.

He groaned as he pulled the blankets to his face.

Again?

For fucking real!?

**Notes for the Chapter:**

> "Medi Medi you said that you were going to be busy IRL. Why are you updating to fast?" 
> 
> Well I am in the process of moving, but I'm also trying to find a job. So I need to set up "camp" for a little bit in between trips of moving things down. Working on this (IE a whole new AU) without needing to reference previous continuity. These are pretty fast to type up and get up since I have the idea and most of the chapters are self contained, unlike "With Hope" and "SHSL!Monsters" 
> 
> So I hope you don't mind the minor wait on those and enjoy these "mostly" self contained Multi-chapter fics. ^^


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